HUT74440A - Herbicidal aryl and heteroaryl pyrimidines and herbicidal compositions containing them as ingredients - Google Patents

Abstract

This invention relates to novel aryl and heteroaryl pyrimidine derivatives, shown below, substituted at the 2- and 4-position of the pyrimidine ring, their use as herbicides and agricultural compositions comprising the same. In formula (I), W is a substituted phenyl or a substituted 5- or 6-membered aromatic heterocyclic ring wherein one or two atoms of said ring are selected from oxygen, nitrogen and sulfur; W being substituted by at least R; R is CO2R<4>, CHO, CONH-O-CH2CO2R<4>, COSR<4>, CO2CHR<5>OCOR<6> or CH=NOR<4>; R<1>, R<2>, R<4>, R<5>, R<6> are as defined in the application; m = 1 or 2.

Description

HERBICIDAL ARILY AND HETEROARYL PYRIDIDINE DERIVATIVES AND HERBICIDAL AGENTS CONTAINING THESE DERIVATIVES

The present invention relates to novel aryl and heteroarylpyrimidine derivatives, their use as herbicides and herbicidal compositions containing such derivatives.

A number of pesticidal aryl and heteroaryl pyrimidine derivatives are known. No. 4,752,524. U.S. Patent No. 4,051,798, for example, describes 2- (2-alkyl-6-aryl-pyrimidin-4-yl) -nicotinic acid herbicides. and the pyridylpyrimidine derivatives having fungicidal activity. Harris et al. Disclose heterocyclic diaryl compounds that control plant growth [Aust. J. Chem., 32, 669-679 (1979)].

We have recognized that there are certain pyridine rings 2 and

4-substituted aryl and heteroarylpyrimidine derivatives having both herbicidal and plant growth inhibitory activity, which can be used both before and after emergence to control annual and perennial grasses and broadleaf weeds.

The terms "herbicide" and "herbicide" as used herein refer to the inhibition or modification of undesirable plant growth. We consider inhibition and modification to be any deviation from natural development, such as complete eradication of plants and retardation of their growth, leaf loss and dehydration, growth control, dwarf growth, stalking, growth promotion, and foliage burn. 85594-2703-PT is sufficient to exert herbicidal activity

The term &quot; 2 volumes &quot; is used to designate amounts that provide such inhibition or modification when applied to the undesired plants themselves or to their site of growth. The term "plant" may be used in all cases of germinating seeds, growing seedlings or adult vegetation, including roots and above-ground parts of plants.

More particularly, the present invention relates to aryl and heteroarylpyrimidine derivatives having the general formula (I):

- W is a phenyl group substituted with at least one R substituent or an aromatic heterocyclic group containing one or two heteroatoms substituted with at least one R substituent, one or two heteroatoms selected from oxygen, nitrogen and / or sulfur, wherein R is CHO or a group, having CO ₂ R ⁴ , CO ₂ NHH-O-CH 2 -CO ₂ R ⁴ , COSR ⁴ , CO ² CHR ⁵ OCOR ⁶ or,

In the general formula CH = N-OR - R is hydrogen, alkali metal cation, alkaline earth metal cation, ammonium cation, substituted ammonium cation, phosphonium cation, alkylphosphonium cation, trialkylphosphonium cation, trialkylsulfoxonium, trialkylsulfoxonium, a group, an alkoxyalkyl group, an optionally substituted phenyl group or an optionally substituted phenylalkyl group;

- R 4 is hydrogen or alkyl; and θ

- R is alkyl, alkenyl, halo · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · ·

- 5 alkyl-alkyl, alkoxy-alkyl, optionally substituted phenyl or optionally substituted phenyl-alkyl;

- is Ar, (Z) Y-Ar or ZAr, where «X.

- Ar is an optionally substituted aryl or heteroaryl group: phenyl, pyridyl, piperonyl, naphthyl, indolyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzoxazolyl, benzothiazolyl, phenanthryl, pyridyl, pyridyl, anthranilyl, pyrimidinyl, pyrazinyl, thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, and thiadiazolyl, with the addition of the following substituents: haloalkyl, haloalkylthio, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy, haloalkoxy, alkoxyalkyl, cyano, nitro, alkoxy-carbonyl group, amino, alkylamino, dialkylamino and hydroxy;

- Y is oxygen, sulfur or NH;

- the meaning of the Z substituents is independent of each other

- 4enyl - optionally substituted C 1 -C 3 alkyl, C 2 -C 4 alkynyl or optionally substituted C 2 -C 4 alkenyl, with the proviso that the substituents may be alkyl and halogen; and - x is 0, 1 or 2; furthermore

the substituents R are independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, haloalkyl, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkoxy, alkoxyalkyl, cyano, a nitro group, an amino group, an alkylamino group, a dialkylamino group, a hydroxyl group, or a group having the general formula C 1 -C 4 wherein R is already substituted; and

- m is 1 or 2 with the following restrictions:

(i) ha r! W is a substituent other than that represented by formula (a); and (ii) when R ^{1 is} optionally substituted phenyl and W is a group of formula (b),

R is other than alkyl and alkenyl.

As used herein, the term alkyl refers to straight or branched chain alkyl or cycloalkyl groups having up to 6 carbon atoms. This is the definition

Refers to, for example, the alkyl chain of haloalkyl groups and both alkyl chains of alkoxyalkyl groups. Alkenyl groups have from 2 to 6 carbon atoms.

Suitable halogens include fluorine, chlorine, bromine and iodine. The haloalkyl groups may contain one or more halogen atoms. The term alkali metal cation refers to the cation of metals in subgroup 1A of the periodic table, particularly sodium and potassium. The term alkaline earth metal ions refers to a cation of magnesium, calcium, strontium or barium.

The term phenylalkyl refers to phenyl substituted alkyl. Optionally substituted phenyl, optionally substituted phenylalkyl, and optionally substituted phenoxy, respectively, on one or more ring carbon atoms optionally substituted with alkyl, halogen, alkoxy, alkenyl, cyano and / or nitro. , refers to a phenylalkyl group and a phenoxy group.

The term "substituted ammonium cation" refers to a C 1 -C 20 alkyl group, a di (C 1 -C 20 alkyl) group, a tri (C 1 -C 20) alkyl group, a tetra (C 1 -C 20) alkyl group, a hydroxy (C 1 -C 5 alkyl) group, di (hydroxy-C1-C5 alkyl), tri (hydroxy-C1-C5 alkyl), (C1-C5 alkoxy) (C1-C5 alkyl), hydroxy (1-5 alkyl). refers to an ammonium cation substituted with C 1-5 -alkoxy) -C 1-5 -alkyl or C 1-5 -alkoxy-carbonylC 1-5 -alkyl.

A preferred subgroup of compounds of formula (I) are those compounds wherein W is phenyl, pyridyl, thienyl, furyl or isothiazolyl.

Preferably, W is a group wherein, in the formulas (c), (d), (©) »(f) or (g), the substituents F are independently selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkoxy, cyano, alkoxycarbonyl, alkylamino, dialkyl,

6

-amino, or -N (R) -CO-R, and n is 1, 2, 5 or 4.

Particularly preferred groups are those compounds of formula (I) wherein (i) W is a group of formula (d);

(ii) R is CC ^ CHO or R ⁴ CONH-OC ^ Cogr ^4, COSR ^4, C0 ₂ GHR ⁵ OCOR ⁶ or CH = N0R ⁴ radical;

(iii) ^R1 is Ar, (Z) YAR or locking, wherein

Ar is optionally substituted phenyl, pyridyl, naphthyl, indolyl, piperonyl, quinolyl, benzoxazolyl, anthranil or phenanthryl;

- Y is oxygen, sulfur or NH;

- Z is optionally substituted C 1 -C 3 alkyl, C 2 -C 4 alkynyl or optionally substituted alkenyl, with the proviso that the substituents may be alkyl and halogen; and

- x is 0, 1 or 2;

4 (iv) R is hydrogen, CC1R, or alkoxy;

(ν) R is hydrogen or halogen;

(vi) R is hydrogen, alkali metal cation, alkaline earth metal cation ion, ammonium cation, substituted ammonium cation, phosphonium cation, alkylphosphonium cation, trialkylsulfonium cation, trialkylsulfoxoniumalkoxy, alkyl, -alkyl, optionally substituted phenyl or optionally substituted phenylalkyl;

(vii) R is hydrogen or alkyl; and (viii) Β ^δ is alkyl, alkenyl, haloalkyl, alkoxyalkyl, optionally substituted phenyl or optionally substituted phenylalkyl.

6

Preferably, R is substituted with GC ^ CHROCOR or R is hydrogen, alkyl, alkali metal cation, alkaline earth metal cation, ammonium cation, substituted ammonium cation, phosphonium cationium, trialkylsulfonium

CC3R containing the cation cation and R

optionally substituted phenyl, pyridyl, naphthyl, quinolyl, piperonyl, or (Z) -O-phenyl or Z-phenyl, wherein Z is (C 1 -C 3) alkyl, (C 2 -C 4) alkynyl or (C 2 -C 4) alkenyl; is 1.

More preferably, R is hydrogen, sodium cation, ammonium cation, potassium cation, calcium,

a CC4R containing cation, magnesium cation, trimethylsulfonium cation, trimethylsulfoxonium cation or isopropylammonium cation; R is phenyl or substituted phenyl substituted with methyl, methoxy, chloro, fluoro, amino, haloalkoxy, nitro and haloalkyl; R is hydrogen, alkoxy or CClR.

A further subgroup of compounds of formula (I) which can be used with very good results is (i) where W is (c);

(ii) R is CHO, or CH2R14, CONH-O-CH2CO2R4, COSr1 COO, CHR2OOR3, or CH = NOR ^Z2 ';

(iii) r! wherein Ar is (Z) YAr or ZAr (Ar is optionally substituted phenyl, pyridyl, naphthyl, indolyl, piperonyl, quinolyl, benzoxazolyl, benzothiazolyl, anthranilyl or phenanthryl); Y is oxygen, sulfur or NH, the substituents Z being, independently, optionally substituted C 1 -C 4 alkyl, C 2 -C 4 alkynyl, or optionally substituted C 2 -C 4 alkenyl, with the proviso that the substituents are alkyl and halogen atoms; and x is 0, 1 or 2);

4 (iv) R is hydrogen, G ₂ R, alkoxy or alkyl;

(v) R 4 is hydrogen or halo (n is present);

1 or 2);

(vi) R is hydrogen, an alkali metal cation, an alkaline earth metal cation, an ammonium cation, a substituted ammonium cation, a phosphonium cation, an alkylphosphonium cation, a trialkylsulfonium group, an alkylthio, a trialkylsulfoxenium, a trialkylsulfoxenium, alkyl, optionally substituted phenyl or optionally substituted phenylalkyl;

(vii) R 1 is hydrogen or alkyl;

(viii) R ⁶ stands for a alkyl, alkenyl, haloalkyl, alkoxyalkyl, optionally substituted phenyl or optionally substituted pyrimidine derivatives having a substituted phenylalkyl.

6

Preferably R is COgCHR'OCOR or R is hydrogen, alkyl, alkali metal cation, alkaline earth metal cation, ammonium cation, substituted ammonium cation, phosphonium cation, triall phosphonium cationium, trialkylsulfonium

CC1R containing 1; And R is optionally substituted phenyl, pyridyl, naphthyl, quinolyl, piperonyl, (Z) -O-phenyl or Z-phenyl, wherein Z is (C 1 -C 3) alkyl, (C 2 -C 4) alkynyl, or May be C4-alkenyl and x is 1.

It is even more preferred that R is hydrogen, sodium, ammonium, potassium, calcium, magnesium, trimethylsulfonium, trimethylsulfoxonium or isopropylammonium ·

and R is phenyl optionally substituted with substituents selected from the group consisting of methyl, methoxy, chloro, fluoro, amino, haloalkoxy, nitro and haloalkyl, and R is hydrogen.

Another preferred subgroup is the compounds of formula (I)

- R represents a hydrogen atom, an ammonium cation, a sodium cation, a potassium cation, a calcium cation, a magnesium cation, a trimethylsulfonium cation, a trimethylsulfoxonium cation or an isopropylammonium cation;

a C0 ₂ R group having the general formula Ban;

- R 4 represents Ar, (Z) Y-Ar or Z Ar, where> x>

- Ar is phenyl, pyridyl, naphthyl, indolyl, piperonyl, quinolyl, benzoxazolyl, benzothiazolyl or phenanthryl, respectively, with the proviso that the above groups may be optionally substituted with halogen, alkyl, alkyl, -alkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy, haloalkoxy, alkoxyalkyl, cyano, nitro, alkoxycarbonyl, amino, alkyl amino, dialkylamino, and hydroxy;

- Y is O, S or NH, preferably O;

—Z is optionally substituted C 1-3 alkyl, C 2-4 alkynyl, or optionally substituted C 2-4 alkenyl, with the proviso that the substituents may be alkyl and halo; and - x is 0, 1 or 2.

Further, a preferred subgroup is the compounds of formula (I)

- W is a group of formula (e), (f) or (g) wherein - R is CHO or GOgR ⁴ , GONH-O-Cl ₂ CO ₂ R ⁴ , COSR ⁴ , CO ₂ CHR ⁵ OGO R ⁶ , or GH = N0R ⁴ radical; and - the substituents R may be hydrogen and / or halogen;

- R 4 is Ar, Z is OAr or ZAr where Ar is optionally substituted phenyl, pyridyl, naphthyl, indolyl, piperonyl, quinolyl, benzoxazolyl, benzothiazolyl or phenanthryl; and p

- the R substituents are hydrogen.

As mentioned above, the present invention also relates to herbicidal agents which, in addition to an agriculturally acceptable diluent, contain a compound of formula (I) in an amount sufficient to exert herbicidal activity.

The following process is generally applicable to the preparation of the compounds of the invention.

Suitably substituted 1- (aryl or heteroaryl) -3- (N, N12)

-dimethylamino) -prop-2-en-1-one is heated in a suitable solvent such as methanol in the presence of an appropriately substituted amidine or amidine hydrochloride and optionally a base such as sodium methoxide. This gives the substituted 4- (aryl or heteroaryl) -pyrimidine derivative.

The amidine derivatives required to carry out the process can be purchased or prepared from commercially available starting materials. For example, amidine derivatives were prepared by R.S. Garigipati (Tetrahedron Letters, 51, 1969 (1990)) by reacting appropriately substituted nitriles with chloromethylaluminum amide in toluene.

The following examples further illustrate the process for preparing the compounds of the present invention.

Example 1 ^a ) Preparation ^of 1- [5- (Methoxycarbonyl) pyridin-2-yl] -5- (N, N-dimethylamino) -prop-2-en-1-one

A suspension of 2-acetylpyridine-5-carboxylic acid (27.1 g, 164 mmol) and toluene (200 mL) was maintained at reflux to remove water by azeotropic distillation. After collecting about 20 ml of distillate, the solution was cooled to ambient temperature and 54 ml of N, N-dimethylformamide dimethylacetal was added dropwise. The resulting brown solution was refluxed for 5 hours and then allowed to cool. The cooled solution was concentrated in vacuo to a small volume. The residue was treated with diethyl ether and stirred overnight. The precipitated orange crystals, m.p. 126-129 ° C, are separated by vacuum filtration. The compound so prepared was found to be 1- [5- (methoxycarbonyl) - 13 · · · · · · · · · · · · · · ··

pyridin-2-yl] -3- (N, N-dimethylamino) prop-2-en-l-one.

b) Preparation of 2- [4- (2-Phenyl) pyrimidinyl] -3-pyridinecarboxylic acid (Table 1, Compound 7)

2.00 g (8.54 mmol) of 1- [3-methoxycarbonyl) pyridin-2-yl] -5- (Ν, Ν-dimethylamino) -prop-2-en-1-one, To a solution of benzamidine hydrochloride hydrate (50 g, 8.54 mmol) and dry methanol (100 mL) was added 4.0 mL of 25% sodium methoxide in methanol. The resulting dark solution was refluxed for 6 hours, during which time about half of the methanol was allowed to evaporate. The solution was then stirred at ambient temperature for 72 hours and then evaporated to dryness in vacuo. The residue was partitioned between ethyl acetate and 0.5 M aqueous sodium hydroxide. The aqueous layer was washed once with ethyl acetate and then acidified to pH J with concentrated hydrochloric acid. The precipitated solid was collected by vacuum filtration and dried under vacuum at 50 ° C for 1 hour. A tan solid, m.p. 169-170 [deg.] C., is obtained which according to NMR and mass spectrum gives the desired 2- [4- (2-phenyl) -pyrimidinyl] -5-pyridinecarboxylic acid.

c) Preparation of 2- [4- (2-Phenyl) -pyrimidinyl] -3-pyridinecarboxylic acid monosodium salt (Table 1, Compound 1) in ml of methanol: 1.00 g (3.61 mmol) of 2- [4- (2-Phenyl) -pyrimidinyl] -3-pyridinecarboxylic acid was suspended and 0.82 ml (3.01 mmol) of 25% sodium methoxide in methanol was added to the resulting slurry. The resulting solution was stirred for 5 minutes and then concentrated in vacuo. The solid foam which remained after evaporation gave 2- [4- (2-phenyl) -pyrimidinyl] -5-pyridinecarboxylic acid, monosodium salt, according to 1 H NMR and mass spectrum.

Example 2

a) Preparation of 2- [4- [2- (5-Chloro-phenyl) -pyrimidinyl] -5-pyrimidinecarboxylic acid (Compound 14 of Table 1)

4.29 g (18.52 mmol) of 1- [5- (methoxycarbonyl) pyridin-2-yl] -5- (N, N-dimethylamino) -prop-2-en-1-one, 5.50 g (18.52 mmol)

To a solution of 5-chlorobenzamidine hydrochloride and 150 ml of methanol is added 8.5 ml of a 25% solution of sodium methoxide in methanol. The resulting brown solution was refluxed for about 6 hours while allowing about half of the methanol to evaporate. The solution was allowed to cool and concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The insoluble solid was filtered off with suction and dissolved in 1M aqueous sodium hydroxide. The resulting solution was acidified to pH 5 with concentrated hydrochloric acid. The resulting precipitate was collected by suction filtration and dried. This gave a tan solid, m.p. 165-166 ° C, which according to 1 H-NMR and mass spectrum gave the desired 2- [4- [2- (5-chlorophenyl)] - pyrimidinyl] -5-. pyridinecarboxylate.

5 »example

Preparation of 2- [4- [2- (4-Fluorophenyl) pyrimidinyl] -5-pyridinecarboxylic acid (Compound 16 of Table 1)

5.88 g (25.1 mmol) of 1- [5- (methoxycarbonyl) pyridin-2-yl] -5- (N, N-dimethylamino) -prop-2-en-1-one, To a solution of 4-fluorobenzamidine (5.47 g, 25.1 mmol) in methanol (150 mL) was added

- 12.1 mL (55 mmol) of 25% sodium methoxide in methanol. The resulting solution was stirred, heated to reflux, and allowed to evaporate a certain amount of methanol. After 2 hours, the heating was turned off and the reaction mixture was stirred overnight at ambient temperature.

The solution is heated to reflux for an additional four hours. The reaction mixture was then cooled and concentrated in vacuo. The residue was taken up in water and the resulting mixture was washed twice with ethyl acetate. The solid precipitate formed in the ethyl acetate wash was separated by vacuum filtration. The solid was dissolved in 1M sodium hydroxide solution and the resulting solution was acidified with concentrated hydrochloric acid. The resulting solid was collected by vacuum filtration. The white solid obtained after vacuum drying had a melting point of 194-196 ° C.

The original aqueous layer was acidified with concentrated hydrochloric acid and the solid separated by vacuum filtration. The solid was recrystallized from ethyl acetate to give a light tan solid melting at 195-196 ° C. NME and mass spectral data show the two solids prepared as described, both of which are the desired 2- [4- [2- (4-fluorophenyl) pyrimidinyl] -3-piperidinecarboxylic acid.

Example 4

Preparation of 2- [4- [2- (3-Chloro-4-methyl-phenyl)] -pyrimidinyl] -3-piperidinecarboxylic acid (Compound 24 of Table 1)

3.4-7 g (14.8 mmol) of 1- [3- (methoxycarbonyl) pyridin-2-yl] -3- (N, N-dimethylamino) -prop-2-en-1- solution of 3-chloro-4-methylbenzamidine (2.50 g, 14.8 mmol) in methanol (150 mL).

• ·

6.8 ml of 25N sodium methoxide in methanol are added. The resulting solution was refluxed for 2 hours but allowed to distil about half of the methanol. The reaction mixture was stirred at ambient temperature over a weekend and then refluxed for a further 4 hours. After cooling, the reaction mixture was concentrated in vacuo. The residue was treated with 1 M aqueous sodium hydroxide solution and the insoluble solid was removed by filtration. The filtrate was washed with ethyl acetate, acidified to pH 5 with concentrated hydrochloric acid, and extracted three times with ethyl acetate. After evaporation in vacuo, a tan solid is obtained. The insoluble solid resulting from said filtration was slurried at 50 ° G in 1M aqueous sodium hydroxide solution until dissolved, and the resulting solution was washed with ethyl acetate, filtered and acidified with concentrated hydrochloric acid. The ethyl acetate extracts were washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The light tan solid thus obtained is combined with 0.20 g of tan solid obtained as described above. The product obtained after the combination was NMR and mass spectrum of the desired 2- [4- [2- (3-chloro-4-methylphenyl)] pyrimidinyl] -3-pyridinecarboxylic acid ·

Example 5

Preparation of 2- [4- [2- (3-Chloro-phenoxy) -methyl] -pyrimidinyl] -3-pyridinecarboxylic acid (Table 1, Compound 22)

2.66 g (11.4 mmol) of 1- [3- (methoxycarbonyl) pyridin-2-yl] -3- (N, N-dimethylamino) -prop-2-en-1-one, To a solution of 2.10 g (11.4 mmol) of 5-chlorophenoxyacetamidine and 100 ml of methanol was added 17 -

5 x 2 mL (22.8 mmol) of 25% sodium methoxide in methanol is added. The resulting solution was slowly refluxed overnight while allowing about half of the methanol to evaporate from the reaction mixture, which was then concentrated in vacuo. The residue was partitioned between 0.5 M aqueous sodium hydroxide and ethyl acetate. The aqueous layer was washed with ethyl acetate followed by concentrated hydrochloric acid to pH = 5, ^r is acidified. The crude solid was collected by vacuum filtration and purified by silica gel chromatography. The eluent was eluted with a 2: 1 by volume mixture of ethyl acetate and methanol. 155 to 158 ° C, a tan solid is obtained, which according to 1 H NMR and mass spectrum, gives the desired 2- [4- [2- (5-chlorophenoxy) methyl] pyrimidinyl (-5- pyridinecarboxylate.

Example 6

Preparation of 2- [4- [2- (2-Phenyl) ethenyl] pyrimidine] -5-pyridinecarboxylic acid (Table 1, Compound 26)

2.72 g (11.6 mmol) of 1- [5- (methoxycarbonyl) pyridin-2-yl] -5- (N, N-dimethylamino) -prop-2-en-1-one, To a solution of 1.86 g (11.6 mmol) of cinnamidine (cinnamic acid amidine) and 5θ mL of methanol are added 8.0 mL of 25% w / w sodium methoxide in methanol. The resulting dark colored solution was heated to reflux for 2 hours. After stirring for 72 hours at ambient temperature, the reaction mixture was treated with 2.0 ml of acetic acid and evaporated to dryness in vacuo. The residue was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The aqueous layer was washed twice with ethyl acetate, acidified to pH 4 with concentrated hydrochloric acid, and filtered to remove the crude solid. The filtrate was extracted with ethyl acetate and concentrated in vacuo. The brown oily residue was combined with the crude solid and the product was purified by preparative thin layer chromatography on silica gel. The slurry was a mixture of dichloromethane, methanol and acetic acid (180: 20: 1 by volume). This gives a tan solid which melts at 167 ° C with decomposition. NMR showed this material to be the desired 2- [4- [2- (2-phenyl) ethenyl] pyrimidinyl] -3-pyridinecarboxylic acid.

Example 7

Preparation of 2- [4- [2- (1-Naphthyl)] -pyrimidinyl] -3-pyridinecarboxylic acid (Table 1, Compound 27)

4.46 g (19 mmol) of 1- [3- (methoxycarbonyl) pyridin-2-yl] -3- (N, N-dimethylamino) -prop-2-en-1-one, 3, To a solution of 1-naphthamidine (24 g, 19 mmol) in methanol (50 mL) was added sodium methoxide (25 mL, 25% in methanol, 13 mL, 57 mmol). The resulting dark solution was refluxed for 18 hours. The reaction mixture was then treated with 3.5 ml of acetic acid and concentrated in vacuo. The residue was chromatographed on silica gel. A 4: 1 by volume mixture of ethyl acetate and methanol was used as the slurrying agent. The product containing fractions was evaporated in vacuo, slurried in ethyl acetate, filtered, and the filtrate concentrated in vacuo. In this way, only a slightly contaminated solid is obtained, which is purified by repeated chromatography on silica gel. Ethyl acetate, methanol and acetic acid as the eluent · ·········································································································································································································································

- 19: 90: 10: 1 by volume. This gives a tan solid which melts at 205-207 ° C.

According to the NMR spectrum, this solid was the desired 2- [4- [2- (1-naphthyl)] - pyrimidinyl] -5-pyridinecarboxylic acid.

Examples of compounds and other compounds obtainable by the methods described are set forth in the following Tables 1 and 2 with the various substituents.

Table 1: Compounds of Formula I &apos;

Number of compounds W R R ¹ Melting point, ° C First (H) formula Na ^ CO phenyl > 270 Second (H) formula C0 ₂ Na ⁺ p-aminophenyl 192.5 to 196 5th (B) formula CO 4 Na ⁴ 2-naphthyl 260 (b) 4th (H) formula co ₂ h 4-pyridyl 287-289 5th (H) formula C0 ₂ Na ⁺ 1-naphthyl 125 (b) 6th (H) formula C0 ₂ Na ⁺ 4-pyridyl 284 (b) 7th (H) formula co ₂ h phenyl 169-170 8th (H) formula 0 C0 ₂ Na ⁺ p-methoxyphenyl > 270 9th (H) formula -c-nh-och ₂ - -CO ₂ CH ₅ phenyl 134 to 140.5 10th (H) formula co ₂ h p-chlorophenyl 185 (b) 11th (H) formula C0 ₂ Na ⁺ p-chlorophenyl > 500 12th (H) formula C0 ₂ Na ⁺ styryl 265 (b) 15th (H) formula co ₂ ch ^ m-chlorophenyl 118-119 14th (H) formula co ₂ h m-chlorophenyl 165-166 15th (H) formula C0 ₂ Na ⁺ m-chlorophenyl > 280 16th (H) formula co ₂ h p-fluorophenyl 195-196

• ·

- Table 1 (continued 1)

The WR R ^ point, ° C serial number of the readings

17th (H) formula C0 Na ⁺ p-fluorophenyl > 280 18th (H) formula co ₂ h p-chlorophenyl 160-163 19th (H) formula C0 ₂ Na ⁺ p-chlorophenyl 64.5 to 123.5 20th (H) formula co ₂ h m-nitrophenyl 235-237 (b) 21st (H) formula C0 Na ⁺ m-nitrophenyl 282 (b) 22nd (B) formula co ₂ h of formula (i) 155-158 23rd (H) formula C0 Na ⁺ of formula (i) 245-251 24th (H) formula co ₂ h of formula (j) 168-172 25th (H) formula C0 ₂ Na ⁺ of formula (j) > 280 26th (H) formula co ₂ h styryl 183-186 27th (H) formula co ₂ h 1-naphthyl 205-207 28th (H) formula co ₂ h 2-naphthyl 156-162 29th (H) formula co ₂ h k 194-195 50th (H) formula C0 ₂ Na ⁺ k > 280 51st (H) formula co ₂ h p- (trifluoromethyl) - 233-237 phenyl 32nd (H) formula C0 ₂ Na ⁺ p- (trifluoromethyl) - > 280 phenyl 33rd (H) formula co ₂ h Of formula (1) 212-216 34th (H) formula co ₂ h m-fluorophenyl 170-172 35- (H) formula co ₂ h m- (trifluoromethyl) - phenyl 36th (H) formula co ₂ h m 75 (b) 37th (H) formula co ₂ h of formula (n) 115 38th (H) formula co ₂ h of formula (s) 169.5 to 175.5

Table 1 (continued 2)

The chemical- leaks: serial number W B B ¹ Melting point, ° C 59th (H) formula co ₂ h of formula (t) 85-95 40th (H) formula co ₂ h (u) 205-212 41st (She) formula co ₂ h m-chlorophenyl 42nd (She) formula co ₂ h p-fluorophenyl 4J. (P) formula co ₂ h phenyl 44th (She) formula CO ₂ H 3-pyridyl 45th (R) formula co ₂ h p-chlorophenyl 46th (She) formula co ₂ h styryl 47th (V) formula go for ₂ h phenyl 48th (V) formula co ₂ h 3-pyridyl 49th (P) formula C0 ₂ Na ⁺ of formula (n) 50th (P) formula co ₂ h 5-pyridyl 51st (X) formula go for ₂ h phenyl 52nd (Y) formula CO ₂ H phenyl 55th (H) formula co ₂ h of formula 218-221 54th (X) formula C0 ₂ Na ⁺ p-fluorophenyl > -500 55th (X) formula C0 ₂ Na ⁺ p-chlorophenyl t-500 56th (X) formula co ₂ h p-fluorophenyl 154-167 57th (X) formula co ₂ h p-chlorophenyl 215-214 58th (Z) i co ₂ h p-chlorophenyl 169-175 59th (Z) i C0 ₂ Na ⁺ p-chlorophenyl 5 x 300 60th (H) formula C0 ₂ Na ⁺ (u) 210-217 61st (X) formula co ₂ h m-fluorophenyl 127-154 62nd (X) formula co ₂ h m-chlorophenyl 118-127

»· · · · · · · · ·

- Table 1 (continued on page 5)

Serial number of compounds W R R ¹ Melting point, ° C 65th (X) formula C0 Na ⁺ m-fluorophenyl > 500 64th (X) formula COgNa ⁴ · m-chlorophenyl > 300 65th (H) formula C0 ₂ Na ⁺ of formula (t) 185-195 66 · (X) formula C0 Na ⁺ 5-pyridyl 2 * 300 67th (H) formula co ₂ h aa 238-240 68th (H) formula C0 Na ⁺ of formula (ab) > 260 69th (X) formula C0 ₂ Na ⁺ of formula (ac) 176 (b) 70th (H) formula C0 ₂ Na ⁺ aa > 250 71st (H) formula C0 ₂ Na ⁺ of formula (ad) 267.5 (b) 72nd (H) formula C0 Na ⁺ ae 73rd (H) formula co ₂ h af 210-215 74th (H) formula C0 ₂ Na ⁺ af > 290 75th (H) formula co ₂ h of formula (g) 90-92 76th (H) formula C0 ₂ Na ⁺ of formula (g) > 250 77. (H) formula co ₂ h m ethoxyphenyl 138-140 78th (H) formula C0 Na ⁺ m ethoxyphenyl 210-212 79th (H) formula co ₂ h of formula (ah) 243.5 to 247 80th (H) formula C0 ₂ Na ⁺ of formula (ah) > 300 81st (H) formula co ₂ h ai 107-110 82nd (H) formula C0 ₂ Na ⁺ ai > 300 85th (H) formula C0 ₂ Na ⁺ m-bromophenyl > 300 84th (H) formula co ₂ h of formula (aj) 138-141 85th (H) formula C0 ₂ Na ⁺ of formula (aj) > -300 86th (H) formula co ₂ h of formula (ak) 180-182

- 23 Table 1 (continued 4) ·· * · ··

Number of compounds w R R ¹ Melting point, ° C 87th (B) formula C0 Na ⁺ of formula (k) > 300 88th (B) formula co ₂ h m-methoxyphenyl 95-98 89th (H) formula C0 ₂ Na ⁺ m-methoxyphenyl 250-252 90th (B) formula co ₂ h 3-quinolyl 131-135 91st (B) formula C0 Na ⁺ 3-quinolyl > 300 92nd (B) formula co ₂ h of formula (g) 264.5 to 271 93rd (H) formula C0 ₂ Na ⁺ of formula (g) > 300 94th (B) formula co ₂ h (al) 95-97 95th (B) formula C0 ₂ Na ⁺ (al) 222-225 96th (B) formula co ₂ h of formula (am) 86.5 to 91.5 97th (B) formula C0 Na ⁺ of formula (an) 288.5 to 291.5 98th (B) formula co ₂ h p- (methylthio) phenyl 211-213 99th (B) formula C0 Na ⁺ p- (methylthio) phenyl > 300 100th (B) formula C0 ₂ H of formula (an) oily One hundred and first (B) formula co ₂ h ao) 269-270 102nd (B) formula C0 ₂ Na ⁺ ao) > 300 103rd (B) formula C0 Na ⁺ p-hydroxyphenyl 1 > 275 104th (B) formula C0 Na ⁺ ap ^ 290 105th (B) formula C0 ₂ Na ⁺ ar > 300 106th (B) formula C0 ₂ Na ⁺ of formula (as) > 300 107th (B) formula C0 Na ⁺ of formula (at) 235 108th (B) formula C0 'Na ⁺ (au) 278-281 109th (B) formula C0 Na ⁺ of the formula (ax) > 290 110th (B) formula co ₂ h ay 209.5 to 213.5

Table 1 (5, continued) ····

The compounds are: serial number W R R ¹ Melting point, ° C 111th of formula (h) C0 ₂ Na ⁺ ay > 300 112th of formula (h) C0 Na ⁺ of formula (az) 5-300 115th of formula (h) C0 Na ⁺ ba 233-236 114th of formula (h) C0 ₂ Na ⁺ bb > -300 115th of formula (h) C0 Na ⁺ (be) 115-119 116th of formula (h) 00 "Na ⁺ bd 244 (b) 117th of formula (h) C0 Na ⁺ m-methylphenyl 278.5 to 281 118th of formula (h) C0 Na ⁺ 1-isoquinolyl • Ø250 119th of formula (h) C0 ₂ Na ⁺ (be) > 250 120th of formula (h) C0 Na ⁺ bf 5-290 b = decomposes Table 2: (1 ^) general compounds The chemical- melting tickets R R ² R ¹ mp, ° C number 121st C0 ₂ Na ⁺ OH phenyl 122nd C0 ₂ Na ⁺ 00 ₂ Na ⁺ phenyl 125th C0 ₂ Na ⁺ oc ₂ h ₅ phenyl 124th C0 ₂ Na ⁺ and ₅ phenyl 125 0 C0Na ⁺ οο ₂ η ^ phenyl

Example 8

The weighed test compounds are dissolved in a stock solution which is dissolved in a 1: 1 (v / v) mixture of acetone and deionized water containing 0.5 booster. The stock solutions thus obtained can be diluted to form solutions for spray application in a single application of 4.0 kg / ha, 1.0 kg / ha or 0.25 kg / ha. Spray broths are applied with a low-gauge sprayer set to spray 1000 liters of liquid per hectare.

During pre-emergence studies, each dose of herbicide is applied in a single band above the core zone. The contents of the flower pots containing seeds are then covered with soil and the plants are transplanted in a greenhouse · After 7 and 19 days of treatment, the effects of each herbicide are visually evaluated.

In post-emergence studies, the test compound is applied at various doses to the foliage of selected seedlings grown on seed. Weeds of different species were then placed in a greenhouse and the results were visually evaluated 1, 7 and 19 days after treatment. The weed species tested are listed in Table 5 ·. Some of the compounds of formula I have been found to be effective in both pre-emergence and post-emergence applications. The herbicidal effect is expressed as the percentage of weed damage: total weed control is defined as 100% damage. In pre-emergence and post-emergence screening of the compounds produced, weights greater than 80% can be obtained from the various test weeds.

eradication at 1, 5, 5, 1.0 kg / ha,

7th-12th and 19-24. s. agents.

For grasses, all tested weed species can be eradicated by more than 75% at 60 kg, 65%, 68%, 71%, 78%, 85%, 84% and 94% at 1.0 kg / ha. compounds. However, it should be noted that this list does not include all the test results obtained and does not include the serial numbers of all the compounds that achieve the given herbicide limit.

Table J: Names of weeds tested

Common name Latin name (genus, race) Silk mallow Abutilon theophrasti Hairy pigtail Amaranth meat retroflexus White mustard Sinapis alba Black dress Solanum nigrum wild oats Avena fatua Fluffy Rye Bromus tectorum barnyardgrass Echinochloa crus-galli foxtail Setaria viridis

*

METHODS OF APPLICATION

The compounds of the formula I can be applied in a conventional manner: they are applied to the weeds or to their place of application in an effective amount, usually from 1 g / ha to 10 kg / ha.

The compounds of the invention are broad-leaved and spicy

- 27 • ···· ··· can be used to control weeds by pre-emergence application as well as pre-emergence and post-emergence application. The compounds of the present invention may be selective in certain crop cultures and may therefore be used in herbicide control, for example, but not limited to, corn, cotton, soybean and soybean and rice crops.

The optimal application of the compounds of formula (I) can be readily determined by one of ordinary skill in the art by routine assays, such as greenhouse testing and small-field field trials. The optimum application mode. depends on the compound employed, the effect sought (higher doses of active ingredients are required to achieve phytotoxic effects than to control plant growth), the conditions of treatment, and other such factors. Generally, a satisfactory phytotoxic effect can be achieved if the compounds of the formula I are present in the range of 0.001 to 5.0 kg / ha, preferably 0.05 to 2.5 kg / ha, more preferably 0.01 to 2.5 kg / ha. dose.

The compounds of formula (I) may advantageously be combined with other herbicidal agents to extend the range of weeds to be released. For example, the compounds of the present invention may be used in combination with herbicides such as carbamates, thiocarbamates, chloroacetamide derivatives, triazine derivatives, dinitroaniline derivatives, benzoic acid derivatives, glycerol ethers, pyridazinone derivatives and uracil derivatives to broaden the herbicidal spectrum. . stem glaze wedges.

The compounds of formula (I) may be formulated with suitable agricultural herbicidal compositions which are also included in the present invention by the addition of agricultural diluents. These compositions may contain, in addition to the compounds of the formula I, other active substances, for example other herbicides or antidotes, or compounds having antifungal, insecticidal or insecticidal action. The herbicidal compositions of the present invention can be formulated using conventional diluents in both solid and liquid formulations, such as wettable powders, emulsifiable concentrates, granules or microcapsules. These agents may be prepared in conventional manner, for example, by mixing the active ingredient with a diluent and, optionally, other formulating agents, such as surfactants.

Agro-acceptable additives may be used in the preparation of herbicides, for example to enhance the action of the active ingredient, to reduce foaming and to prevent clumping and corrosion.

The term diluent as used herein may refer to any liquid or solid agriculturally acceptable substance that can be added to the active ingredient to provide a form that is easier or more effective to use, that is, to provide usability and the desired potency. Examples of such diluents are talc, kaolin, diatomaceous earth, xylene and water.

The term "surfactant" is used herein to mean agriculturally acceptable substances which

they render the composition emulsifiable, spreadable, wettable, dispersible or otherwise modify its surface properties. Suitable surfactants are, for example, sodium lignin sulfonate or lauryl sulfate.

In particular, spraying agents such as water dispersible concentrates and wettable powders contain surfactants such as wetting agents and dispersing agents such as formaldehyde naphthalene sulfonate, ethoxylated alkyl phenol and ethoxylated fatty alcohol.

The herbicidal compositions of the present invention generally contain from 0.01 to 99% of active ingredient, from 0 to 20% by weight of an agriculturally acceptable surfactant and from 0.1 to 99x99% of solid or liquid diluent (s). The active ingredient is at least one compound of formula (I) or a mixture of compound (s) of formula (I) and other active ingredient (s). Concentrated dosage forms of the agents of the present invention generally contain from 2 to 95, preferably from 10 to 90, active ingredients.

The following are representative examples of the composition and method of preparation of the herbicidal agents of the present invention in which the amounts are expressed in parts by weight.

Example A)

Production of soluble powder

The water-soluble salts of the active compounds of the invention are ground in a hammer mill until the particles pass through a 0.149 mm mesh screen. The powder thus obtained is easily dissolved in water and sprayed as a solution.

• ·

Example B)

Production of wettable powder

25 parts of the active compounds of the present invention are mixed and ground with 25 parts of fine synthetic silica, 2 parts of lauryl sulfate, 3 parts of sodium lignin sulfonate and 45 parts of finely divided kaolin. Grinding is continued until the average particle size is about 5 microns. The wettable powder thus obtained is diluted with water to the desired concentration.

Example C)

Preparation of Water Dispersible Granules A part of the water-insoluble acid of the invention is wet-milled in a solution containing 10 parts of MARASPERSE Ν-22 (sodium lignin sulfonate) and 5 parts of water until an average particle size of 5 microns is reached. The resulting slurry is spray-dried in a NIRRO MOBILE MINOR operating at an inlet temperature of 150 ° C and an outlet temperature of 70 ° C. The granules so prepared are readily dispersible in water and can be used in dispersed form.

Example D)

Preparation of a microcapsule suspension

a) 0.38 parts Vinol 205 to (partially hydrolyzed poly (vinyl alcohol) was dissolved in 79 parts of water _t ^.

b) 3.75 parts of an organic soluble acid of the invention are dissolved in 3.75 parts TENNECO 500-100 (in the same boiling point as the xylene in an aromatic solvent).

To the solution thus obtained is added 0.63 parts of sebacic acid chloride

51 and 0.88 parts of PAPI 133 [poly (methylene isocyanate)].

c) 1.89 parts of peperazine and 0.30 parts of sodium hydroxide are dissolved in 12.60 parts of water.

The premix a) is poured into an emulsifier of about 1 liter, and the premix b) is added with stirring and the resulting mixture is subjected to shear for 60 seconds or until a droplet size of 10-20 microns is reached. Subsequently, premix c) was added immediately, stirring was continued for 3 hours, and the mixture was neutralized with acetic acid. The resulting capsule suspension may be diluted with water prior to spraying.

Example E)

Preparation of the Emulsifiable Concentrate The organic acid-soluble acid of the invention is dissolved in 79 parts TENNECO 500-100 with 2 parts TOXIMUL BHF and 6 parts TOXIMUL S. TOXIMULs are matching pairs ”: both TOXIMULs contain anionic and nonionic emulsifiers. The stable solution is spontaneously emulsified in water and the resulting emulsion can be sprayed.

Claims (10)

Claims Aryl and heteroarylpyrimidine derivatives having the general formula (I) - W is a phenyl group substituted with at least one R substituent or an aromatic heterocyclic group containing one or two heteroatoms substituted with at least one R substituent, one or two heteroatoms selected from oxygen, nitrogen and / or sulfur, wherein R is CHO or a group, having C0 ₂ R ⁴ , 00ΝΗ-0-σΗ 2-σ02Β ⁴ , COSR ⁴ , CO ² CHR ⁵ 0C0 R ⁶ or CH = N-OR eben - R is hydrogen, alkali metal cation, alkaline earth metal cation, ammonium cation, substituted ammonium cation, phosphonium cation, alkylphosphonium cation, trialkylphosphonium cation, trialkylsulfoxonium, alkyl, alkoxyalkyl, optionally substituted phenyl or optionally substituted phenylalkyl; - R is hydrogen or alkyl; es - Βθ is alkyl, alkenyl, haloalkyl, alkoxyalkyl, optionally substituted phenyl or optionally substituted phenylalkyl; - R ^ is Ar, (Ζ) _χ Υ-Ατ or ZAr, where ·· ·· - Ar is one of the following optionally substituted aryl or heteroaryl groups: phenyl, pyridyl, piperonyl, naphthyl, indolyl, quinolyl, isoquinolyl, quinoxalinyl. , quinazolinyl, benzoxazolyl, benzothiazolyl, phenanthryl, pyridyl N-oxide, anthranilyl, pyrimidinyl, pyrazinyl, thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, thiazolyl, isothiazolyl, with the proviso that the above groups may be substituted with the following substituents: phenoxy, halogen, alkyl, alkenyl, haloalkyl, haloalkylthio, alkylthio, alkylsulfinyl, alkylsulfonyl a group, an alkoxy group, a haloalkoxy group, an alkoxyalkyl c soport, cyano, nitro, alkoxycarbonyl, amino, alkylamino, dialkylamino, and hydroxy; - Y is oxygen, sulfur or NH; - the substituents Z are, independently, optionally substituted C 1-3 alkyl, C 2-4 alkynyl, or optionally substituted C 2-4 alkenyl, with the proviso that the substituents may be alkyl and halogen; and - x is Ο, 1 or 2; furthermore - R is independently hydrogen, halogen, alkyl, alkenyl, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy, alkoxyalkyl, cyano, a nitro group, an amino group, an alkylamino group, a dialkylamino group, a hydroxyl group, or a group having the formula CC1R wherein R is substituted with one or more substituents; and - m is 1 or 2 with the following restrictions: (i) when R ^{1 -} is phenyl, W is only a substituent other than that of formula (a); and (ii) when R 4 is optionally substituted phenyl and W is a group of formula (b), R is other than alkyl and alkenyl. 2. The aryl and heteroaryl pyrimidine derivatives according to claim 1, wherein W is phenyl, pyridyl, thienyl, furyl or isothiazolyl. 3. The aryl and heteroarylpyrimidine derivatives according to claim 2, wherein W is a group of formula (c), (d), (e), (f), or (g) in the general formula R is the substituent independently of one another hydrogen, halogen, alkyl, haloalkyl, alkoxy, cyano, alkoxycarbonyl, alkylamino, dialkylamino or -N (R 6) -CO-R 6 - general R 4 and g R is as defined in claim 1, n is 1, 2, 3 or 4 and R is as defined in claim 1. 4. The aryl and heteroarylpyrimidine derivatives according to claim 3, which have the formula: - W is a group of the formula (d) in which, 4 - R is a GHO group or CClR; C0NH-0-CH ₂ C0 ₂ R ^4, COSR ^4, C0 ₂ ⁵ CHR ⁶ 0G0R and CH = NOR; And the radicals R 1-4 may be hydrogen or halogen; - R * is Ar, (Z) YAr or ZAr, wherein - Ar is optionally substituted phenyl, pyridyl, naphthyl, indolyl, piperonyl, quinolyl, benzoxazolyl, anthranil or phenanthryl; 2 4 and the substituents R may be CO ₂ R, hydrogen, and alkoxy. 5. The aryl and heteroarylpyrimidine derivatives according to claim 4, which have the formula: - W is substituted with an R substituent of the formula CO ₂ CHR ₂ O CO ₂ R ⁶ or CO ₂ R ⁴ where R is hydrogen, sodium cation, ammonium ion, potassium cation, calcium cation, magnesium cation, trimethylsulfonium cation, trimethylsulfoxo a cation or an isopropylammonium cation; And R ^{1 is} Z-phenyl optionally substituted with phenyl, pyridyl, naphthyl, quinolyl, piperonyl or Z in which C 1 -C 3 alkyl, C 2 -C 4 alkynyl or C 2 -C 4 alkenyl, or (Z) - O-phenyl, where x is 1. 6. The aryl and heteroarylpyrimidine derivatives according to claim 3, which have the formula: - W is a group of formula (c) in which Z 1 - R are CHO or CO ₂ R, GONH-O-CH ₂ CO ₂ R ⁴ , GOSR ⁴ , CO ₂ CHR ⁵⁰ O CO ⁶ or 4, CH = NOR general group; es - the substituents R may be hydrogen or halogen; R is Ar, Z is YAr or ZAr, where Ar is optionally substituted phenyl, pyridyl, naphthyl, indolyl, piperonyl, quinolyl, benzoxazolyl, benzothiazolyl, anthranyl or phenanthryl; and the substituents R may be hydrogen, alkyl groups, alkoxy groups and CO ₂ R groups. 7. The aryl and heteroarylpyrimidine-57 derivatives according to claim 4, which have the formula: - W is substituted with an R substituent of the formula CC ^ CHR ^ OCOR ^ or CO ₂ R ⁴ where R is hydrogen, sodium cation, ammonium cation, potassium cation, calcium cation, magnesium cation, trimethylsulfonium cation, trimethylsulfoxonium cation. or isopropylammonium cation; - the R substituents are hydrogen; and R 4 is optionally substituted phenyl, pyridyl, naphthyl, piperonyl, quinolyl, Z-phenyl or (Z) -O-phenyl, where x is 1. 8. The aryl and heteroarylpyrimidine derivatives according to claim 3, which have the formula: - W is a group of formula (e), (f) or (g) where - R is CHO or CC 1 R, CONN-O-CH ₂ CO ₂ R ⁴ , COSR ⁴ , CO ₂ CHR ⁵ OCO ⁶ , or 4, CH = NOR general group; x - and the substituents R 1 may be hydrogen and halogen; R6 is Ar, Z is Ar or ZAr, wherein - Ar is - optionally substituted phenyl, pyridyl, naphthyl, indolyl, piperonyl, quinolyl, benzoxazolyl, benzothiazolyl or phenanthryl; and the B substituents may be hydrogen. 9. The aryl and heteroarylpyrimidine derivatives according to claim 5, which have the formula: - W is substituted with R having 4, CC ^ R in general R is hydrogen, sodium cation, ammonium cation, potassium cation, calcium cation, magnesium cation, trimethylsulfonium cation, trimethylsulfoxonium cation or isopropylammonium cation; And R 4 is Ar, (Z) Y-Ar or Z Ar, where - Ar is - optionally substituted phenyl, pyridyl, naphthyl, indolyl, piperonyl, quinolyl, benzoxazolyl, benzothiazolyl, anthranil or phenanthryl, noting that the optional substituents are halogen, alkyl, alkenyl, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy, haloalkoxy, alkoxyalkyl groups, cyano groups, nitro groups, alkoxycarbonyl groups, amino groups, alkylamino groups, dialkylamino groups and hydroxy groups; - Y is oxygen, sulfur or NH; · · · · · · · · · · · · · · · · · · · · · · · ··· - Z is optionally substituted C 1 -C 3 alkyl, C 2 -C 4 alkynyl, or optionally substituted C 2 -C 4 alkenyl, with the proviso that the substituents may be independently alkyl or halogen; And x represents 0, 1 or 2. 10. Herbicidal agents which contain, in addition to agriculturally acceptable diluents, sufficient amounts of the compounds according to claim 1 to produce herbicidal activity.